Water → HCID 58836075, compound

HRID 600156Notes

Reaction equation

HRID 600156 reaction equation
[C:1]1([CH3:23])[CH:6]=[CH:5][C:4]([C:7]2[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]=2[C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)=[CH:3][CH:2]=1.C1C(=O)N([Br:31])C(=O)C1.O>C1COCC1>[Br:31][C:13]1[CH:14]=[CH:15][C:9]2[C:8]([C:16]3[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=3)=[C:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:23])=[CH:2][CH:3]=3)[S:11][C:10]=2[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 12649526HCID 12649526, compound

Product 1

HCID 58836075HCID 58836075, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.5 g (1 eq, 7.9 mmol) of 2,3-di-p-tolyl-benzo[b]thiophene and 14 g (10 eq, 79 mmol) of NBS were dissolved in 200 ml of THF in a 500 ml-round-bottomed flask and stirred for 6 hours. 50 ml of water was added to the solution to terminate the reaction, and the organic phase was extracted using brine and methylene chloride. The extracted organic phase was dried using anhydrous magnesium sulfate and filtered to remove the solvent. A resulting solid was recrystallized using methylene chloride and hexane, dissolved in a small amount of THF, and separated using column chromatography (silica and hexane) to obtain 2.5 g (71%) of a yellow solid.

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionthe organic phase was extracted
  4. customThe extracted organic phase was dried
  5. filtrationfiltered
  6. customto remove the solvent
  7. customA resulting solid was recrystallized
  8. dissolutiondissolved in a small amount of THF
  9. customseparated

Sources & evidence

ORD record
ord-41fc4f82d11f44cca4a55cbc4a034888
Source dataset
uspto-grants-2011_03
Patent number
US07901793B2

Reaction notes

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